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For my thesis I am looking to expand a part of it to include experimental means of calculating ring strain, thus far I have calorimetry covering heats of combustion and hydrogenation as well as thermogravimetric analysis but I have found little else on ACS/other sources, and was wondering if anyone has sources on hand or recommended readings?

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  • $\begingroup$ One option is to do this computationally. You could calculate the strain energy of ring systems by comparing the energy of a strained ring to that of some unstrained reference structure. $\endgroup$
    – Melanie Shebel
    Commented May 26 at 19:02
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    $\begingroup$ Are you working on just carbocyclic rings or some heterocyclic as well? $\endgroup$
    – Mathew Mahindaratne
    Commented May 27 at 0:59
  • $\begingroup$ I am working on a combination of the two. $\endgroup$
    – nking1390
    Commented May 27 at 14:04

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The title of your question says "Experimental determination of ring strain energy," but I think you understand you cannot find ring strain experimentally. It is a relative term. Only you can experimentally find is either heat of combustion or formation energy of various organic compounds. Then you can calculate extra energy in the molecule by comparing those values with that of "strain-free molecule (reference molecule). Based on your reference molecule, the value on strain energy differs (that's why it is a relative term). You would understand my concept well if you review Ref.1 and 2 (vide infra), which are listed to respond your request.

Also, as Melanie Shebel suggested in her comment to your question, it is not bad idea to do this computationally. You can follow this method using the computation done in Ref. 3. Sited references in Ref.3 provided some valuable heat of formation values for rings you may be interested in (e.g., see Ref.4).

References:

  1. Arthur Greenberg and Joel F. Liebman, In Strained Organic Molecules (Organic Chemistry: A Series of Monographs, Volume 38); Academic Press: New York, NY, 1978, 311–365 (ISBN: 0-12-299550-3).
  2. Joel F. Liebman and Arthur Greenberg, “A survey of strained organic molecules,” Chem. Rev. 1976, 76(3), 311–365 (DOI: https://doi.org/10.1021/cr60301a002).
  3. Todor Dudev and Carmay Lim, “Ring Strain Energies from ab Initio Calculations,” J. Am. Chem. Soc. 1998, 120(18), 4450–4458 (DOI: https://doi.org/10.1021/ja973895x).
  4. H. K. Eigenmann, D. M. Golden, and S. W. Benson, “Revised group additivity parameters for the enthalpies of formation of oxygen-containing organic compounds,” J. Phys. Chem. 1973, 77(13), 1687–1691 (DOI: https://doi.org/10.1021/j100632a019).
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